EP1436017B1 - A process for preparing a gel element - Google Patents
A process for preparing a gel element Download PDFInfo
- Publication number
- EP1436017B1 EP1436017B1 EP02767697A EP02767697A EP1436017B1 EP 1436017 B1 EP1436017 B1 EP 1436017B1 EP 02767697 A EP02767697 A EP 02767697A EP 02767697 A EP02767697 A EP 02767697A EP 1436017 B1 EP1436017 B1 EP 1436017B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- premix
- perfume
- crosslinking agent
- process according
- components
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 239000002304 perfume Substances 0.000 claims description 89
- 239000003431 cross linking reagent Substances 0.000 claims description 62
- 229920000642 polymer Polymers 0.000 claims description 61
- 239000007788 liquid Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 34
- 239000000499 gel Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 150000001299 aldehydes Chemical class 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 10
- 239000005062 Polybutadiene Substances 0.000 claims description 9
- 229920002857 polybutadiene Polymers 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 150000003138 primary alcohols Chemical class 0.000 description 5
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 2
- JJWWUTCHOAKZPR-UHFFFAOYSA-N 4-methylpent-4-en-2-yl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)CC(C)=C JJWWUTCHOAKZPR-UHFFFAOYSA-N 0.000 description 2
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 2
- 239000009261 D 400 Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010636 coriander oil Substances 0.000 description 2
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 2
- 229930008394 dihydromyrcenol Natural products 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010642 eucalyptus oil Substances 0.000 description 2
- 229940044949 eucalyptus oil Drugs 0.000 description 2
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 229920001002 functional polymer Polymers 0.000 description 2
- 239000010648 geranium oil Substances 0.000 description 2
- 235000019717 geranium oil Nutrition 0.000 description 2
- 239000001851 juniperus communis l. berry oil Substances 0.000 description 2
- 239000001469 lavandula hydrida abrial herb oil Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000010668 rosemary oil Substances 0.000 description 2
- 229940058206 rosemary oil Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- YZTGPAICMPNIAQ-UHFFFAOYSA-N 1-(3-acetylcyclohex-2-en-1-yl)ethanone Chemical compound CC(=O)C1CCCC(C(C)=O)=C1 YZTGPAICMPNIAQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 229920013646 Hycar Polymers 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- IGONDPIZPLAUSP-UHFFFAOYSA-N cyclohexene oxane Chemical compound O1CCCCC1.C1=CCCCC1 IGONDPIZPLAUSP-UHFFFAOYSA-N 0.000 description 1
- VWTINHYPRWEBQY-UHFFFAOYSA-N denatonium Chemical compound [O-]C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C[N+](CC)(CC)CC(=O)NC1=C(C)C=CC=C1C VWTINHYPRWEBQY-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 1
- -1 oleyl amines Chemical class 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
- A61L9/12—Apparatus, e.g. holders, therefor
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
- A61L9/048—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating air treating gels
Definitions
- the present invention relates to a process for preparing a gel element comprising a perfume and to a process for preparing an air freshening device comprising such a gel element.
- Such devices may simply fragrance the air, or may be used to mask bad odours.
- This device comprises a gelled element resulting from the cross-linking between a functionalised liquid polymer and a cross-linking agent in the presence of a perfume base.
- a liquid functionalised polymer is mixed with a cross-linking agent in the presence of a perfume.
- the polymer crosslinks in the presence of the perfume to form a gel which encloses the perfume, preferably in a three-dimensional network.
- Such a gel can be formed in a recess in a substrate to form an air freshener device, or can simply be used as a block.
- This gel has an attractive appearance.
- a large proportion of perfume base for example up to 90 wt %, especially 60 to 90 wt %, may be used which provides a gel element of a small size.
- the volume of crosslinking agent is small compared with the volume of perfume and polymer.
- the crosslinking agent may be used in an amount of up to 2 vol% with respect to the total volume of components which are mixed together before gelling. While it is practicable to mix the perfume and polymer together to form a homogeneous mixture and then mix in the crosslinking agent, we have found that such an arrangement is not completely satisfactory because it is difficult to control the flow of the crosslinking agent in view of its relatively small volume.
- the gelling time of the mixture i.e. the time required for a gel which does not flow to be formed, tends to rise over time. This can cause significant problems as the manufacturing shift progresses, especially at the end of a shift when a machine is operating.
- the gelling time of the mixture increases such that it is longer than the time that the containers containing the perfume element are on the production line, the gel may not have solidified to an acceptable extent and may still at least partly be in liquid form when the containers are removed from the line. This liquid can spill out of the containers leading not only to wastage but also to other problems such as fouling of the production line and local environment.
- the present invention seeks to overcome this problem by providing a process in which the setting time of the mixture is reasonably constant over the time that a production machine is likely to operate, for example an eight hour shift or the length of time that the mixtures are stored before they are used, which is typically about four hours.
- the present invention provides a process for preparing a gel element comprising a perfume which comprises:
- Perfumes usually contain components which react with either or both of the liquid functionalised polymer and the crosslinking agent. Accordingly in the process of the present invention the liquid functionalised polymer and crosslinking agent are mixed with different parts of the perfume, namely perfume components A and perfume components B, before they are mixed together. Thus the liquid functionalised polymer and crosslinking agents are not simply mixed with the same perfume composition. Instead the final perfume composition for the gelled element is determined, and different components of the composition are mixed with the liquid functionalised polymer and with the crosslinking agent. It has surprisingly been discovered that by ensuring an appropriate separation of perfume components, the above problem can be solved to a practical extent or even completely avoided. It is, of course, possible for some individual components which do not substantially react with either the liquid functionalised polymer or the crosslinking agent to be present in both perfume components A and perfume components B..
- the perfume used in the process of the present invention is typically an anhydrous perfume, for example comprising less than 1 wt% water, especially less than 0.5 wt % water, more especially less than 0.1 wt % water and preferably comprising no water, and comprises a mixture of different ingredients.
- the perfume may simply provide a fragrance or it may provide a deodorising effect. While the precise ingredients of any particular perfume are often the trade secret of a Fragrance Supplier, it is well known that perfume ingredients are typically volatile compounds such as esters, alcohols, aldehydes and ketones. We have found that functionalised polymers and crosslinking agents can react with certain perfume ingredients.
- the rate of reaction may be relatively slow, so while this may not be a problem at the start of the production run, after the perfume ingredients have been mixed with the functionalised polymer and/or crosslinking agent for some time, for example after a few hours, some reaction will have occurred with some of the perfume components. This may undesirably affect the perfume so its fragrance is not constant over the full production run. Furthermore it will use up some of the functionalised polymer and/or crosslinking agent, which results in a reduction in the concentration of reactive sites of the functionalised polymer and/or the crosslinking agent after the production run has proceeded for some time. We have found that this leads to the increased setting time.
- the liquid functional polymer possesses one or more functional groups.
- the crosslinking agent possesses two or more complimentary functional groups.
- the mixtures of these two compounds gives, in the presence of a perfume base, a reaction product enclosing the perfume base which can then emanate to the atmosphere to provide an air freshening effect.
- To obtain a three-dimensional network it is, however, necessary for the liquid functional polymer to have at least two functional groups per molecule.
- the liquid functionalised polymer is one which is liquid at room temperature (20°C) and which generally has a viscosity of not more than 5,000 poise at 25°C, preferably from 250 to 1,000 poise.
- the liquid functionalised polymer should be soluble in the perfume base.
- One or more liquid functionalised polymers may be used.
- Suitable functional groups are, for example, carboxylic acid, anhydride or acid chloride groups as well as amine and alcohol groups.
- the polymer can be produced by adding functional groups to any polymer which is capable of functionalisation, or the polymer can be one which inherently contains functional groups, either pendent on the main chain, optionally with intervening spacer groups, or in the main chain.
- Preferred polymers which can be functionalised are polyolefins, particularly those derived from mono- or di-olefins containing, prior to functionalisation, at least one and preferably more than one vinyl group.
- the polymer is a derivative of butadiene, isoprene or chloroprene.
- the polymer is maleinised polybutadiene which may, for example, have a molecular weight of from 5000 to 20,000, or maleinised polyisoprene which may, for example, have a molecular weight of from 200,000 to 500,000.
- Such polymers are commercially available materials. Examples are disclosed in EP-A-23,084. A preferred polymer is sold under the trademark Lithene by Synthomer.
- a particularly preferred Lithene polymer is Lithene N4-9000 10MA, which is a maleinised polybutadiene wherein the molecular weight of the polybutadiene before maleinisation is about 9000 and which contains 10 parts of maleic anhydride per 100 parts of polybutadiene.
- Lithene N4-B-10MA has also been found to be particularly suitable.
- the crosslinking agent possesses two or more complementary functional groups to the functional groups on the liquid functionalised polymer.
- the complementary functional groups may be, for example, carboxylic acid, anhydride or acid chloride derived groups or amine or alcohol groups.
- the crosslinking agents may have amine or alcohol functions, and vice versa.
- the crosslinking agent contains two, three or more functional groups. Preferably, however, it contains only two functional groups.
- the crosslinking agent should be soluble in the perfume base.
- One or more crosslinking agents may be used.
- suitable crosslinking agents are dihydroxy polybutadiene, alkoxylated primary amines, alkylpropyldiamines having an ethoxylated or propoxylated fatty aliphatic chain, diethanolamine, diethylenetriamine, polyoxyalkylenediamines and alkoxylated primary fatty amines.
- the crosslinking agent may comprise one or more diamines and/or triamines, in particular one or more polyoxyalkylene amines, in particular diamines and triamines, such as polyethoxy diamines and triamines and/or polypropoxy diamines and triamines.
- Suitable ethoxylated primary amines are oleyl amines possessing two moieties of ethylene oxide per molecule.
- alkylpropyldiamines having an ethoxylated or propoxylated higher aliphatic chain are those sold under the trademark Dicrodamet by Croda Chemicals Limited.
- polyoxyalkylene diamines and/or triamines examples include polypropoxy diamines, polypropoxy triamines and polyethoxydiamines, particularly those sold under the trademark Jeffamine by Huntsman Corporation, for example Jeffamine D-400, Jeffamine D-2000, Jeffamine T-403 and Jeffamine EDR-148.
- crosslinking agents are oleylamines or cocoamines having 2 to 5 ethylene oxide units per molecule, such as those sold under the trademark Crodamet by Croda Chemicals Limited, for example Crodamet O2 and Crodamet C5.
- Additional useful crosslinking agent is polybutadiene having a hydroxylic function known as HFPB, obtainable from Revertex ltd. This crosslinking agent is especially suitable for use with maleinised polybutadiene.
- Another suitable crosslinking agent is an amine terminated liquid butadiene/acrylonitrile copolymer, such as Hycar CTBN 1300 x 21, obtainable from B.F. Goodrich.
- the functionalised liquid polymer and crosslinking agent can be used in any molar ratio. Desirably, however, the molar ratio is from 3:1 to 0.5:1, preferably from 1.5:1 to 1:1.5, more preferably about 1:1, based on the molar ratio of the functional groups which are present. In general it is preferred to minimise the amount of unreacted functionalised polymer and crosslinking agent in the gelled element.
- Catalysts can be included in premix A, premix B or in a further premix to assist in the gel formation.
- catalysts are tertiary amines, for example DAMA 1010 obtainable from Albemarle SA, and Jeffcat TD 100 or Jeffcat DMP, obtainable from Huntsman Corporation
- the mixture which gels comprise up to 90 wt% perfume base, especially 60 to 90 wt%, more especially 75 to 85 wt%, based on the total weight of the mixture. It also desirably comprises 8 to 35 wt%, especially 12 to 25 wt%, more especially 15 to 20 wt%, functionalised liquid polymer, based on the total weight of the mixture, and desirably also comprises 0.5 to 20 wt%, especially 0.5 to 6 wt%, more especially 0.7 to 4 wt%, crosslinking agent, based on the total weight of the mixture.
- premix A can also be included in premix A, premix B or in a further premix.
- Such components can include, for example, additional perfume components, solvents, bitrex and dyes.
- the perfume is a mixture of volatile liquid ingredients of natural or synthetic origin.
- the nature of these ingredients can be found in specialised perfumery books, for example in S. Arctander, Perfume and Flavour Chemicals, Montclair, N.J., USA, 1969.
- an initial step of devising a perfume having the desired fragrance This is a routine operation which can be carried out by a Fragrance House.
- the crosslinking agent which is able to react with some of the perfume components, whereas the liquid functionalised polymer usually does not appreciably react during the timescale of a production shift.
- those components of the perfume which react or are considered likely to react with the crosslinking agent form the basis of premix A.
- the remaining components which do not react or are considered unlikely to react with the crosslinking agent may form premix B.
- liquid functionalised polymer but not the crosslinking agent, is able to react with some of the perfume components, those components of the perfume which react or are considered likely to react with the liquid functionalised polymer form the basis of premix B.
- the remaining components which do not react or are considered unlikely to react with the liquid functionalised polymer may form premix A. Again, it is perfectly possible for some of these components which do not react with the liquid functionalised polymer to be added to premix B.
- premix B Another way of proceeding is to determine the ingredients of the perfume and simply to take those a few of the components which are known not to react with the crosslinking agent to form premix B or which are known not to react with the liquid functionalised polymer to form premix A. All of the other components are then used to form premix A or premix B respectively.
- the aldehydes are capable of reacting with either the liquid functionalised polymer or the crosslinking agent. It is usual, therefore, for substantially all of the aldehydes to be present in premix B or premix A respectively.
- ketones often react with the liquid functionalised polymer or crosslinking agent, although their rate of reaction is less than that of the aldehydes and some ketones do not react for steric reasons.
- alcohols in particular primary alcohols, often react with the liquid functionalised polmyer or crosslinking agent.
- the alcohols or at least the primary alcohols and optionally secondary alcohols and/or tertiary alcohols, are present in the premix A or premix B respectively. It is particularly desirable for the premix A or premix B not to contain aldehydes, and preferably also not to contain ketones, when the liquid functionalised polymer or crosslinking agent, respectively, contains amine groups.
- liquid functionalized polymer is a maleinised polybutadiene and the crosslinking agent is one or more polyoxyalkylene diamines
- aldehydes in particular can react with the crosslinking agent. It is usual, therefore, for substantially all of the aldehydes to be present in premix A.
- ketones also react with the crosslinking agent, although their rate of reaction is less than that of the aldehydes. We have found therefore that it is also desirable for ketones to be present in premix A, which contains the aldehyde components.
- primary alcohols will react with the maleic anhydride moeities of the liquid functionalised polymer and it is usual therefore for substantially all primary alcohols to be present in premix B
- each premix is stable at room temperature (20°C) for at least 2 hours, preferably at least 4 hours, more preferably at least 6 hours and most preferably at least 8 hours.
- premix A and/or premix B may contain some fragrance components which are capable of reacting slowly with the liquid functionalised polymer or crosslinking agent, respectively, but which do not appreciably react within the time that the premixes are stored before use.
- the premix A or premix B it is, of course, possible for the premix A or premix B to contain small quantities of components which react with the liquid functionalised polymer or crosslinking agent, respectively, so long as these do not appreciably reduce the amount of liquid functionalised polymer or crosslinking agent which is available for reaction.
- the reaction only occurs to an extent that the gelling time to achieve a solid, non-flowable gel increases only slightly, for example by up to 20%, preferably up to 10%, more preferably up to 5%.
- the gelling time increases at most to 7 minutes 12 seconds, preferably at most to 6 minutes 32 seconds and more preferably at most to 6 minutes 18 seconds.
- the premix A and/or premix B contain less than 1 wt%, preferably less than 0.5 wt% of components which react with the liquid functionalised polymer or crosslinking agent respectively. More desirably, the premix A and/or premix B contains no aldehydes and/or ketones and/or primary alcohols as appropriate.
- the process of the present invention can surprisingly reduce the formation of undesirable side products which can otherwise be formed during the process.
- certain premixes could become cloudy, and even lack phase stability.
- this was due to certain perfume components, in particular aldehydes, reacting with groups on the liquid functionalised polymer or crosslinking agent, in particular amine groups, especially primary amine groups, to form a substituted imine and water.
- This water is not usually miscible with the anhydrous perfume base and hence the perfume base becomes cloudy. In extreme situations, the water can even form a second phase.
- certain components, such as the substituted imines can precipitate from solution which can cause blockages in the production machinery.
- the process of the present invention surprisingly also overcomes this disadvantage since the in situ formation of water and other components such as imines is substantially avoided.
- the mixture gels i.e. forms a non-flowable solid in step iii in less than 8 minutes during the entire production run, preferably from 4 to 8 minutes, more preferably from 6 to 7 minutes.
- the weight ratio of premix A to premix B is desirably from 2:1 to 8:1, for example from 3:1 to 6:1, especially from 4:1 to 5:1.
- the weight ratio of perfume components A to perfume components B is desirably from 2:1 to 6:1, preferably from 3:1 to 5:1.
- the gel element is desirably formed by adding the mixture of premix A and premix B to a mould, for example a recess in a substrate, and allowing the mixture to gel.
- a mould for example a recess in a substrate
- suitable substrates and forms for the recess are given in WO 00/24434.
- fragrance was prepared: Ingredient % w/w Isobornyl acetate 25.00 Dihydromyrcenol 25.00 tertiary-4-Butylcyclohexyl acetate 15.00 Orange oil terpenes 10.00 Terpinyl acetate 4.00 Eucalyptus oil 4.00 Isopentyrate 3.00 Juniperberry oil 2.50 Lavandin oil 2.00 Allyl Caproate 2.00 Dynascone 1.00 alpha-iso-Methyl ionone 1.00 Geranium oil 1.00 Applinate 1.00 Verdox 1.00 n-Dodecanal 0.50 2-methyl undecanal 0.50 Coriander oil 0.50 Rosemary oil 0.50 Galbanum oil 0.25 2,4-Dimethylformyl-3-cyclohexene 0.20 Oxane (50% in triethylcitrate) 0.05 100.00
- a cross-linking composition was prepared comprising 8.00g Jeffamine D-400 and 4.40g Jeffamine EDR-148.
- Premix A was prepared by mixing 14.26g of Lithene N4-B-10MA and 53.68g of the entire fragrance in a closed 120ml glass powder jar using a magnetic stirrer until the Lithene had completely dissolved.
- Premix A was prepared by mixing 14.55g of Lithene N4-B-10MA and 54.78g of Perfume Component A in a closed 120ml glass powder jar using a magnetic stirrer until the Lithene had completely dissolved.
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Detergent Compositions (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0124728 | 2001-10-16 | ||
GB0124728A GB2381001B (en) | 2001-10-16 | 2001-10-16 | Process for preparing a perfumed gel |
PCT/GB2002/004583 WO2003033038A1 (en) | 2001-10-16 | 2002-10-09 | A process for preparing a gel element |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1436017A1 EP1436017A1 (en) | 2004-07-14 |
EP1436017B1 true EP1436017B1 (en) | 2005-12-28 |
Family
ID=9923861
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02767697A Expired - Lifetime EP1436017B1 (en) | 2001-10-16 | 2002-10-09 | A process for preparing a gel element |
Country Status (15)
Country | Link |
---|---|
US (1) | US7132461B2 (es) |
EP (1) | EP1436017B1 (es) |
CN (1) | CN1292800C (es) |
AR (1) | AR036886A1 (es) |
AT (1) | ATE314100T1 (es) |
AU (1) | AU2002330625B2 (es) |
BR (1) | BR0213307B1 (es) |
CA (1) | CA2464345C (es) |
DE (1) | DE60208409T2 (es) |
ES (1) | ES2256532T3 (es) |
GB (1) | GB2381001B (es) |
MX (1) | MXPA04003601A (es) |
PL (1) | PL203960B1 (es) |
WO (1) | WO2003033038A1 (es) |
ZA (1) | ZA200403125B (es) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7393905B2 (en) * | 2004-12-29 | 2008-07-01 | Weyerhaeuser Company | Crosslinked mixed carboxylated polymer network |
EP1872767A1 (de) * | 2006-06-30 | 2008-01-02 | Ernst Mühlbauer GmbH & Co.KG | Polymerisierbares Dentalmaterial |
US20080015295A1 (en) * | 2006-07-11 | 2008-01-17 | Williams Virgil Ag | Polymeric gel composition and method for making |
MX2009008789A (es) | 2007-02-15 | 2009-08-24 | Procter & Gamble | Composiciones de suministro de agentes beneficos. |
US7700665B2 (en) * | 2007-12-06 | 2010-04-20 | Orlandi Inc. | Fragrant gel polymer system |
WO2010014807A2 (en) * | 2008-08-01 | 2010-02-04 | The Procter & Gamble Company | Perfume compositions comprising functional perfume components |
US20130338056A1 (en) | 2010-07-08 | 2013-12-19 | Sven Dobler | Fragrant gel polymer with solvents |
US8877139B2 (en) | 2010-08-13 | 2014-11-04 | The Procter & Gamble Company | Compositions comprising a functional perfume component mixture |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ289918A (en) * | 1994-08-19 | 1996-11-26 | Firmenich & Cie | Air deodoriser; comprises a gelified element formed by cross-linking a functionalised liquid polymer and a crosslinking ligand in the presence of a deodorising base |
CN1217214A (zh) * | 1997-11-17 | 1999-05-26 | 淄博美华化工有限公司 | 水性固体状空气清新剂 |
PT1121159E (pt) * | 1998-10-22 | 2003-10-31 | Reckitt Benckiser Uk Ltd | Dispositivo para difusao de vapor |
GB2363717B (en) * | 2000-04-19 | 2002-06-19 | Reckitt Benckiser | Coloured anhydrous gel element |
-
2001
- 2001-10-16 GB GB0124728A patent/GB2381001B/en not_active Expired - Fee Related
-
2002
- 2002-10-09 ES ES02767697T patent/ES2256532T3/es not_active Expired - Lifetime
- 2002-10-09 DE DE60208409T patent/DE60208409T2/de not_active Expired - Lifetime
- 2002-10-09 BR BRPI0213307-5A patent/BR0213307B1/pt not_active IP Right Cessation
- 2002-10-09 AU AU2002330625A patent/AU2002330625B2/en not_active Ceased
- 2002-10-09 CN CNB028204646A patent/CN1292800C/zh not_active Expired - Fee Related
- 2002-10-09 EP EP02767697A patent/EP1436017B1/en not_active Expired - Lifetime
- 2002-10-09 WO PCT/GB2002/004583 patent/WO2003033038A1/en not_active Application Discontinuation
- 2002-10-09 AT AT02767697T patent/ATE314100T1/de not_active IP Right Cessation
- 2002-10-09 PL PL368339A patent/PL203960B1/pl unknown
- 2002-10-09 CA CA2464345A patent/CA2464345C/en not_active Expired - Fee Related
- 2002-10-09 MX MXPA04003601A patent/MXPA04003601A/es active IP Right Grant
- 2002-10-09 US US10/492,807 patent/US7132461B2/en not_active Expired - Lifetime
- 2002-10-16 AR ARP020103887A patent/AR036886A1/es not_active Application Discontinuation
-
2004
- 2004-04-23 ZA ZA200403125A patent/ZA200403125B/en unknown
Also Published As
Publication number | Publication date |
---|---|
MXPA04003601A (es) | 2004-07-30 |
ES2256532T3 (es) | 2006-07-16 |
US7132461B2 (en) | 2006-11-07 |
AU2002330625B2 (en) | 2006-11-30 |
EP1436017A1 (en) | 2004-07-14 |
CN1292800C (zh) | 2007-01-03 |
US20050043432A1 (en) | 2005-02-24 |
CN1571681A (zh) | 2005-01-26 |
CA2464345C (en) | 2011-05-24 |
GB0124728D0 (en) | 2001-12-05 |
CA2464345A1 (en) | 2003-04-24 |
DE60208409T2 (de) | 2006-09-07 |
GB2381001A (en) | 2003-04-23 |
PL203960B1 (pl) | 2009-11-30 |
BR0213307A (pt) | 2004-10-13 |
BR0213307B1 (pt) | 2014-12-30 |
ATE314100T1 (de) | 2006-01-15 |
ZA200403125B (en) | 2005-07-27 |
WO2003033038A1 (en) | 2003-04-24 |
GB2381001B (en) | 2003-11-26 |
AR036886A1 (es) | 2004-10-13 |
DE60208409D1 (de) | 2006-02-02 |
PL368339A1 (en) | 2005-03-21 |
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